I have been using Puppy Linux 5.2.8 for a few months now and really like it. My main DE/Window manager is Outbox. I like it because it is simple and easy to configure which is basically what I am looking for after using Macs for many many years. I tried Macpup but am still running into E17 issues that I don't seem to have when using Outbox.

I have never tried tint2. Do you use it instead of fbpanel? How can I try it out in my puppy setup?

Yes i use Tint2 instead of Fbpanel - to use tint2 you will need to disable fbpanel.

I don't have Puppy Linux 5.2.8 installed so im not 100% sure but you can probably get it from the repository - If not try this link + setup guide:
http://www.murga-linux.com/puppy/viewtopic.php?t=64572
Be aware though earlier versions of tint2 is just a panel and system tray, no launchers and no gui customization.

openbox has a much more complete config at ~/.config/openbox/rc.xml, jwm tends to run lighter with a decent set of features native to it. ob has autoraise with delay..

mmrm, here's some old-ish blither for a sample of wm/de/etc - favorite? depends on what I'm up to (afterstep, blackbox, ctwm, dwm, e16, ede, evilwm, fluxbox, flwm, fvwm (95, 262 and 306/crystal), icewm, jwm, mcwm, miwm, a 'bare' openbox, pekwm, qlwm, treewm, twm, wmx and yeahwm as far as I recall - it takes two plogouts to conveniently hold what I currently have on p431 and wary514, remembering the various binds can be tricky for my memory as 'tis )

Because I am using Openbox I should be modifying the rc.xml file, or should I use the GUI options available off the puppy menus? Is there more flexibility modifying the RC file itself? Keep in mind that I am new to all this but find it pretty exciting.

re - use the obconfig gui first (usually in the bottom part of ob's menu), that does the very top part of the rc.xml

Make a backup of rc.xml (say rc.xmlOEM) before editing binds and stuff by hand - the top part will change but the binds are OEM (just in case you futz something you don't have to dig in a ro for the real original or do a pfix=ram )

Then dig into all the key and mouse binds - often there's several ways to perform an action, or several actions that can be performed (depending on the area where you do the input). Be aware of subtle differences like press, on release and so on - it took me awhile to get button2 on titlebar to toggle the shade effect without having to move off the titlebar on release (my scrollwheel died sometime back from using it as button2 on dumb pups that didn't get the imp/s2 protocol, ignoring the perfectly good sidebutton that I usually use). I also put in a bind for rootmenu and clientmenu (just in case the mouse dies, I can still use the kybd to get these)

Test your bind - save your edit to the rc.xml (leave the editor open but min or shade it), do a reconfig (pretty sure that's in the bottom part of obmenu as well - if not, obmenu-refresh does it as last part of its action from the menu). Try the bind, if it works as expected if not, go back to editing (why the editor is left open, eh?)

dept of &etc - at one time I used xfce4 (standard in Gray's NOP puplets and the Saluki branch) .. nice compositing effects but the rest of it can be a rpita (imxho, of course) in aftermarket versions if you use other wms as well. A few dotpets even did some rather odd stuff - one changed the mimetypes (making rox pretty unhappy ). C'est la vie in the just-click-the-dotpet world, sometimes

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